


My first time

by bryboiblue



Category: True stories - Fandom
Genre: Anal Sex, First Time, Loss of Virginity, M/M, Oral Sex
Language: English
Status: Completed
Published: 2021-01-19
Updated: 2021-02-20
Packaged: 2021-03-17 12:01:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,609
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28848741
Author URL: https://archiveofourown.org/users/bryboiblue/pseuds/bryboiblue
Summary: How I met the guy I lost my virginity to and how it happened.This will be in three chapters, with "the event" occurring in the second one.
Relationships: Original Male Character/Original Male Character
Kudos: 3





	1. Chapter 1

It was the summer of my 20th year, and the first summer I spent away from home. I was living in Dupont Circle in Washington D.C. in a two-bedroom apartment with four other guys. Two of them each to a bedroom, and I slept on the futon in the living room.

The apartment had no air conditioning. If you can imagine in what that is like in a city reclaimed from a swamp during the summer, you can guess how uncomfortable and sleepless many of those nights were.

Dupont Circle is basically the gay mecca of D.C. We lived on 22nd Street, just a few steps away from The Fireplace, an always packed gay bar, and basically caddy-corner from a portion of Rock Creek Park, I think known as the P Street Beach, that was a notorious gay cruising and hook-up spot.

My roommates were all straight, and I was not yet out, so you might see how the situation was, at least on occasion, a bit awkward.

I had sucked cock at glory holes at George Washington University where we all had just finished our second year, and occasionally traded blow jobs with my best friend at the time, who was to be my roommate the next semester. I think I had even kissed one of the guys I met in the bathrooms, after sneaking off to a more secluded restroom to service him. 

One Saturday afternoon, I found myself at the Dupont Circle Metro stop, guy-watching, as I was want to do at the time. For those who do not know the area, at the street level, the Metro stop there is a waist-high, circular, concrete wall surrounding two-stage escalators that take you deep under the streets to the actual Metro platform.

As I leaned against the wall, casually watching people going up and down the escalators, I noticed an incredibly gorgeous blond boy, with a backpack slung over one shoulder, doing same from about a quarter of the way around the wall from where I was loitering. We took turns pretending not to seem to be staring at each other for maybe an hour or so. He was about 5-foot-6 and nicely proportioned. At some point, he appeared to try and make a phone call, but seemed not to reach the person he was attempting to contact.

Shortly after that, as the sun was starting to set, he turned and started to walk away, and, in perhaps one of the most stalkerish moments of my life, I followed. And, as he occasionally would look back, I felt encouraged to continue my pursuit, though at first making sure to keep a consistent way back.

Fortunately, the blond boy called my bluff and started walking slower and slower and, very nervously, I closed the distance until I caught up him with after he had turned east onto P Street. 

I do not recall the exact awkward introductions after I reached him, but I learned his name was Dennis, and we started walking around the area. Dennis said that was just visiting the city and was supposed to be meeting up with some friends, but that they had not shown up, and he was unable to reach them. We started looking for somewhere to get a bite to eat, but, although the area is littered with restaurants, they were all too expensive for a pair of college students on a budget.

As darkness fell, we ended up at Rock Creek Park, which by that time was mostly deserted. We lay down next to each other on the grass and kept talking, about our families and this and that. While I very much wanted to touch him and kiss him, our hands stayed firmly planted at our sides, at first, inches away from each other.

At some point our hands tentatively found their way to each other, and we held on for what felt like dear life, taking turns gently running our fingers over the others hand as we conversed.  
Eventually, the time came for that part of the evening to end, and, while I very much wanted to invite him back to my apartment, mere yards away, I knew that we would have no privacy there, and what I wanted to happen very much needed privacy.

To my surprise, Dennis said that he had a hotel room across the Potomac in Arlington and asked if I wanted to go there with him. I eagerly agreed and we took the walk back to the Metro station to make the trip under the river and to the night that awaited us.


	2. And then it happened

**Summary for the Chapter:**

> We get to a motel room and I lose my virginity.

I do not remember waiting for the Metro train or boarding it. 

I do recall us sitting next to each other, making small talk as we took the short ride from DuPont Circle to Alexandria.

At some point, my left hand found its way to Dennis’ right thigh, and it seemed we both had a relieved exhale. His right hand nervously found its way to my left thigh and we quietly, tentatively, and wordlessly inched toward feeling each other up.

A few minutes later, we were disgorged to Alexandria and we started walking, him leading toward our destination.

I learned that he was a theater major, though not much else, but it was a pleasant little stroll in the pale light of streetlamps on a warm summer night.

We got to the motel, where I waited as he checked back in. Apparently, he had not planned to return that night. I did learn his last name, and it has been seared in my mind since.  


We got to his room and sat on the bed for a few minutes, nervously chit-chatting, each afraid to take the obvious next step. Eventually, we started making out and slowly undressed each other.  


We were both young, thin, painfully pale white and not a chest hair to be found. I do not think I had seen a sexier sight in my life. I doubt there was a defined muscle between us, other than maybe my legs.

Here was a gorgeous, naked boy furiously making out with me, our bodies pressed together, our painfully hard cocks trapped between us as we tried to desperately be one.  


In time, I got him on his back and obligingly kissed down his smooth body until I reached promised land. And, oh, what awaited me could not have been more satisfying and terrifying.  


The closest thing I can compare his massive cock to is that of Joey Mills, but straighter and without the bulge, just all around long, thick, and pale, and huge balls in a massive sack, that I do not remember having much hair.

I was enough of a newbie at this point that the idea of trying to deep-throat him didn’t occur to me, and thank the heavens for that. I probably would have choked myself to death. He did not try to force the issue. He just let me do my best to tease his massive member with my mouth and tongue. I would take breaks to lick his big balls and sack before returning my attention to that gorgeous, daunting cock.

Eventually he ended up on top of me, in between my legs, with that huge penis rubbing against my hole. I have never wanted something so much and been so terrified at the same time.  


He stepped away for a moment to grab a bottle of hand lotion from his backpack, and rubbed some around my asshole and onto his cock before asking: “Have you ever done this before?”  


After a few seconds of stammering, I told the lie I most regret to this day in a single syllable: “Yeah.”

“You?” I asked?

“No,” he said, and immediately regret washed over me, but I did not feel as if there was any point to retracting my lie from seconds before, so let it stand.  
That conversation over as quickly as it had begun, he pushed himself into my virgin hole. I was on my back, he between my legs, no real preparation other than the hand lotion on his cock.

It hurt. A lot.

He began to fuck my ass. Not particularly hard, but with long deep strokes, and every one felt as if it was splitting me in half. 

It was glorious and painful. It was a summer night in a former swamp. We worked up a sweat. Dennis, from putting all his energy into the new experience of pounding the heat and tightness of a virgin ass. Me, from enduring the closeness and excruciating pain of having something that huge relentlessly invading me with no control over the situation – and absolutely no desire for it to end.

I know “being split in half” is a description that gets over-used, and hopefully it is only true for people their first time having anal sex, or when encountering a particularly large penis. I got the dubious pleasure of both at the same time. It was all I could do to not cry, and I am fairly sure not a sound came out of me for the several minutes it was going on. 

At a certain point, I began to stretch out enough to start enjoying the experience, and sadly it felt as if it was almost at that same moment that he came deep inside me.

He withdrew, leaving my hole cummy and gaping, feeling as if it would never close again, and collapsed next to me, pressing our sweaty bodies together in passionate, desperate kiss.

The night and encounter were far from over, but that is for the next chapter ….

**Notes for the Chapter:**

> There is more to come from that night and the next day


End file.
